CN104870499B - Copolymer, photosensitive polymer combination containing this copolymer and resin molding - Google Patents
Copolymer, photosensitive polymer combination containing this copolymer and resin molding Download PDFInfo
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- CN104870499B CN104870499B CN201380064319.4A CN201380064319A CN104870499B CN 104870499 B CN104870499 B CN 104870499B CN 201380064319 A CN201380064319 A CN 201380064319A CN 104870499 B CN104870499 B CN 104870499B
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- Prior art keywords
- methyl
- photosensitive polymer
- polymer combination
- copolymer
- ester
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- 229920000642 polymer Polymers 0.000 title claims abstract description 52
- 229920001577 copolymer Polymers 0.000 title claims abstract description 48
- 229920005989 resin Polymers 0.000 title claims description 42
- 239000011347 resin Substances 0.000 title claims description 42
- 238000000465 moulding Methods 0.000 title claims description 21
- -1 hydroxylphenyl ester Chemical class 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000002253 acid Substances 0.000 claims abstract description 28
- 239000012948 isocyanate Substances 0.000 claims abstract description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 230000003252 repetitive effect Effects 0.000 claims abstract description 18
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 39
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 14
- 239000011248 coating agent Substances 0.000 abstract description 12
- 238000003860 storage Methods 0.000 abstract description 8
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 48
- 239000002585 base Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 23
- 239000010408 film Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 6
- 239000011229 interlayer Substances 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000005204 hydroxybenzenes Chemical class 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- 230000010415 tropism Effects 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229960003742 phenol Drugs 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DKJCSMHIPYRALV-UHFFFAOYSA-N methoxymethyl propanoate Chemical compound CCC(=O)OCOC DKJCSMHIPYRALV-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QWRVAXMLZCMVSL-UHFFFAOYSA-N (2,4,6-trihydroxyphenyl)-(3,4,5-trihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC(O)=C(O)C(O)=C1 QWRVAXMLZCMVSL-UHFFFAOYSA-N 0.000 description 1
- ZDROXNKXVHPNBJ-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=C(O)C=CC=C1O ZDROXNKXVHPNBJ-UHFFFAOYSA-N 0.000 description 1
- DIBYQTLCOMYUAP-UHFFFAOYSA-N (2-hydroxy-4-methylphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=CC(C)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O DIBYQTLCOMYUAP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- HWZREQONUGCFIT-UHFFFAOYSA-N (3-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=CC=CC(C(=O)C=2C(=C(O)C(O)=CC=2)O)=C1 HWZREQONUGCFIT-UHFFFAOYSA-N 0.000 description 1
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- ZZYLQDSPBXSJES-UHFFFAOYSA-N (4-hydroxy-2-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(O)C=C1C ZZYLQDSPBXSJES-UHFFFAOYSA-N 0.000 description 1
- FVHMFMMVURPZFE-UHFFFAOYSA-N (4-hydroxy-3-methoxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=C(O)C(OC)=CC(C(=O)C=2C(=C(O)C(O)=CC=2)O)=C1 FVHMFMMVURPZFE-UHFFFAOYSA-N 0.000 description 1
- YHFVEHFXJDCKDF-UHFFFAOYSA-N (4-hydroxy-3-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(O)C(C)=C1 YHFVEHFXJDCKDF-UHFFFAOYSA-N 0.000 description 1
- ZRDYULMDEGRWRC-UHFFFAOYSA-N (4-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O ZRDYULMDEGRWRC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RSJWKIDVVZWYTD-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-2-prop-1-en-2-ylbenzene Chemical class CC(=C)C1=CC=CC=C1C(C)(C)N=C=O RSJWKIDVVZWYTD-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical class OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 1
- UTHVBVWSNXKBGG-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCC(O)COC(=O)C=C UTHVBVWSNXKBGG-UHFFFAOYSA-N 0.000 description 1
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical class OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
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- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
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- IGFDWQYZRPDQQY-UHFFFAOYSA-N 4-[2-[3-[2-[2,4-dihydroxy-5-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenyl]propan-2-yl]-6-[2-(4-hydroxyphenyl)propan-2-yl]benzene-1,3-diol Chemical compound C=1C(C(C)(C)C=2C=C(C=CC=2)C(C)(C)C=2C(=CC(O)=C(C=2)C(C)(C)C=2C=CC(O)=CC=2)O)=C(O)C=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 IGFDWQYZRPDQQY-UHFFFAOYSA-N 0.000 description 1
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- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 1
- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
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- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- RRTCFFFUTAGOSG-UHFFFAOYSA-N benzene;phenol Chemical compound C1=CC=CC=C1.OC1=CC=CC=C1 RRTCFFFUTAGOSG-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- 230000008033 biological extinction Effects 0.000 description 1
- IGKOKEBHGRCHSR-UHFFFAOYSA-N bis(3,4,5-trihydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 IGKOKEBHGRCHSR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VXTQKJXIZHSXBY-UHFFFAOYSA-N butan-2-yl 2-methylprop-2-enoate Chemical compound CCC(C)OC(=O)C(C)=C VXTQKJXIZHSXBY-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- IHHCJKNEVHNNMW-UHFFFAOYSA-N methane;phenol Chemical compound C.OC1=CC=CC=C1 IHHCJKNEVHNNMW-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
- C08K5/08—Quinones
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The copolymer of the present invention contains the repetitive from (methyl) crylic acid hydroxylphenyl ester and the repetitive from the unsaturated compound with blocked isocyanate ester group.Preferably comprise the above-mentioned repetitive from (methyl) crylic acid hydroxylphenyl ester and the above-mentioned repetitive from the unsaturated compound with blocked isocyanate ester group of 10mol%～70mol% of 30mol%～90mol%.The thermochromism transparent, resistance to of the photosensitive polymer combination of the copolymer containing the present invention and excellent electrical property, coating, developability, curable and storage stability are good.
Description
Technical field
The present invention relates to a kind of photosensitive polymer combination, in particular it relates to a kind of photosensitive polymer combination, it is suitable
Form the protecting film of electronic unit, planarization film or the interlayers such as liquid crystal display cells, integrated circuit component, solid-state image pickup
Dielectric film, suitably forms lenticule or microlens array, suitably forms the light scattered reflection film of liquid crystal display cells, tropism control
With projection or interval, suitably form color filter or suitably form optical waveguide.
Background technology
In the past, it was used for preventing TFT type liquid crystal display cells, magnetic head element, integrated circuit component, solid-state image unit in formation
The deterioration of the electronic units such as part or the protecting film of damage, or form the interlayer of insulation between the wiring for making to be configured to stratiform
During dielectric film, use photosensitive polymer combination all the time.Wherein, in the case of liquid crystal display cells, by then passing through
Interlayer dielectric is formed the electrically conducting transparent line layers such as ITO, and forms the operation of liquid crystal orientation film further above and make
Making, therefore interlayer dielectric can be exposed under hot conditions in the formation process of ELD, also can be exposed in shape
Become in the anticorrosive additive stripping liquid controlling used in electrode pattern, it is therefore desirable to they are had sufficient resistance.Therefore, for cambium layer
Between the photosensitive polymer combination of dielectric film, it is desirable to be able to form that developability is excellent and the transparency, thermostability, flatness, attaching
Property, chemical resistance and the resin molding of excellent electrical property.
On the other hand, as chip providing color filters (on-chip such as facsimile machine, electronic copier, solid-state image pickups
Colour filter) imaging optical system or the material of optical system of the joints of optical fibre, employ and there are 3～100 μ
The lenticule of the lens diameter of about m or make the regularly arranged microlens array of these lenticulees.Wherein, for
The CCD element used in digital camera etc., in recent years, more miniaturization while improving pixel count so that every 1 CCD unit
The light receiving area of part reduces.Accordingly, as the means of raising light acceptance amount, attempt being formed lens-shaped on CCD element
Lenticular method.As the lenticule for CCD element, it is known that make photoresist exposure, development form bump maps
Case, by making it flow so that temperature more than glass transition point heats this relief pattern, utilizes surface tension to form hemisphere
The lenticular method of shape.Accordingly, as forming lenticular photosensitive polymer combination, need excellent developability, transparent
Property, fluidity of molten and thermostability, from the point of view of collection luminosity, need high index of refraction.
As above-mentioned photosensitive polymer combination, such as, patent documentation 1 has been recorded a kind of photosensitive resin composition
Thing, it contains (a) unsaturated carboxylic acid and the copolymer of the polymerizable unsaturated compound with epoxy radicals, (b) unsaturated carboxylic acid
With compound and (d) organic solvent that the copolymer of other monoolefine unsaturated compounds, (c) have quinone diazido.
It addition, recorded a kind of photosensitive polymer combination in patent documentation 2, it contains (a) unsaturated carboxylic acid and has epoxy radicals
The copolymer of polymerizable unsaturated compound, (b) phenylethylene and the copolymer of unsaturated carboxylic acid, (c) there is quinone two nitrine
The compound of base and (d) organic solvent.
Having recorded a kind of radiation-sensitive resin composition in patent documentation 3, it contains [A] unsaturated carboxylic acid and has
The unsaturated compound of epoxy radicals and the copolymer of other olefines unsaturated compounds and [B] specifically phenols chemical combination
Thing and the condensation substance of 1,2-naphthoquinone two nitrine sulfamic acid halide.
It addition, recorded a kind of photosensitive polymer combination in patent documentation 4 and 5, it contains unsaturated carboxylic acid and fat
Ring type has copolymer and the 1,2-naphthalene quinone di-azide sulfonic acid ester of the unsaturated compound of epoxy radicals.
The common part of above-mentioned existing photoresist is, all employ the unsaturated carboxylic acid conducts such as methacrylic acid
Manifest alkali-soluble composition.But, these photoresists also have following problem, due to them and the material with phenolic hydroxyl group
Comparing, acidity is high, in addition to the difficult management of developability, with the reactive excellent another side of epoxy radicals, its border of developing
(development margin) and storage stability are insufficient.Although this problem is by using list as part copolymer composition
Olefines unsaturated compound and improved, but due to its be formed scum, therefore be not enough to constitute solution.
It addition, recorded a kind of photosensitive polymer combination in patent documentation 6, it contains (A) hydroxy styrenes and first
The copolymer of base acrylic acid methyl ester., (B) have compound and (C) thermosetting resin of quinone diazido.This resin combination
It is characterised by, uses hydroxy styrenes as manifesting alkali-soluble composition.But, although this photosensitive polymer combination is due to tool
There is phenolic hydroxyl group, be effective as solving the problems referred to above point, but there is the defect coloured because of heating.
It addition, recorded a kind of photosensitive polymer combination in patent documentation 7, it contains and contains hydroxyl as polymeric composition
Base phenyl (methyl) acrylate and have epoxy radicals unsaturated compound copolymer, there is the chemical combination of quinone diazido
Thing.Although the technical problem that this photosensitive polymer combination is able to overcome above-mentioned photosensitive polymer combination to be had and
Develop, but its electrical property and resistance to thermochromism are not enough.
Prior art literature
Patent documentation
Patent documentation 1: JP 2003-330180 publication
Patent Document 2: JP 2005-107314 publication
Patent Document 3: JP 2004-170566 publication
Patent Document 4: JP 2003-76012 publication
Patent Document 5: JP 2005-49691 publication
Patent Document 6: Unexamined Patent 5-158232 publication
Patent Document 7: JP 2007-33518 publication
Summary of the invention
The technical problem to be solved in the present invention
In view of the foregoing, it is an object of the invention to provide a kind of thermochromism transparent, resistance to and excellent electrical property, and
The photosensitive polymer combination that coating, developability, curable and storage stability are good, and provide one to be used for manifesting this
The copolymer of a little characteristics.
Solve the technological means of technical problem
The present inventor etc. conduct in-depth research in order to achieve the above object, found that containing from (first
Base) crylic acid hydroxylphenyl ester repetitive and from the repetitive of the unsaturated compound with blocked isocyanate ester group
Copolymer can realize above-mentioned purpose, thus completes the present invention.
That is, the present invention following [1]～[9] are shown.
[1] a kind of copolymer, it is characterised in that containing from (methyl) crylic acid hydroxylphenyl ester repetitive and from
There is the repetitive of the unsaturated compound of blocked isocyanate ester group.
[2] according to copolymer described in [1], it is characterised in that containing described in 30mol%～90mol% from (first
Base) repetitive of crylic acid hydroxylphenyl ester and the described of 10mol%～70mol% be from having blocked isocyanate ester group not
The repetitive of saturated compounds.
[3] according to copolymer described in [1] or [2], it is characterised in that described in there is the unsaturation of blocked isocyanate ester group
Compound is block (methyl) acrylic acid 2-isocyano group ethyl ester (2-isocyanatoethyl methacrylate).
[4] according to [1] to the copolymer according to any one of [3], it is characterised in that described block is by methyl ethyl ketone
The block that oxime causes.
[5] according to [1] to the copolymer according to any one of [4], it is characterised in that described in there is blocked isocyanate ester group
Unsaturated compound be 2-(O-[1'-methyl propylene amino] carboxyamino) ethyl (methyl) acrylate.
[6] a kind of photosensitive polymer combination, it is characterised in that containing with good grounds [1] to the copolymerization according to any one of [5]
Thing and there is the compound of quinone diazido.
[7] according to the photosensitive polymer combination described in [6], it is characterised in that relative to the described copolymerization of 100 mass parts
Thing, it contains the compound described in 5～60 mass parts with quinone diazido.
[8] according to the photosensitive polymer combination described in [6] or [7], it is characterised in that relative to the composition beyond solvent
Total amount 100 mass parts, it contains the solvent of 30～4000 mass parts.
[9] a kind of resin molding, it is characterised in that [6] are coated with to the photosensitive polymer combination according to any one of [8]
On substrate, it is dried and obtains.
Invention effect
In accordance with the invention it is possible to provide a kind of thermochromism transparent, resistance to and excellent electrical property, and coating, developability,
Curable and the good photosensitive polymer combination of storage stability, and can provide a kind of for manifesting being total to of these characteristics
Polymers.
Detailed description of the invention
Below the photosensitive polymer combination of the present invention is described in detail.
Additionally, in the range of description and claims, (methyl) acrylate is methacrylate or propylene
Acid esters.
In the photosensitive polymer combination of the present invention, the copolymer [A] contained as neccessary composition including: from (a1)
The repetitive of (methyl) crylic acid hydroxylphenyl ester and there is the weight of unsaturated compound of blocked isocyanate ester group from (a2)
Multiple unit.
As the object lesson of (a1) (methyl) crylic acid hydroxylphenyl ester, acrylic acid o-hydroxy ester, propylene can be enumerated
Hydroxylphenyl ester, methyl between hydroxylphenyl ester, acrylic acid para hydroxybenzene ester, methacrylic acid o-hydroxy ester, methacrylic acid between acid
Acrylic acid para hydroxybenzene ester etc..They may be used alone, two or more kinds can also be used in combination.It addition, among them, excellent
Select methacrylic acid para hydroxybenzene ester.
In copolymer [A], preferably comprise 30mol%～90mol% from (a1) (methyl) crylic acid hydroxylphenyl ester
Repetitive, more preferably contain 40mol%～80mol%.If the repetition from (a1) (methyl) crylic acid hydroxylphenyl ester
Unit is less than 30mol%, then alkali solubility may become not enough, on the other hand, if more than 90mol%, possibly cannot be formed good
Good pattern.
(a2) there is the unsaturated compound of blocked isocyanate ester group, easily by making the unsaturation with NCO
Compound reacts with known or well-known block agent, makes NCO carry out block and obtain.As having isocyanide
The unsaturated compound of perester radical, can enumerate (methyl) acrylic acid 2-isocyano group ethyl ester, isopropenyl-alpha, alpha-dimethylbenzyl
Isocyanates etc. have the ethylenically unsaturated compounds of NCO.As block agent, preferably alkyl ketone oximes, phenols,
Alcohols, pyrazoles, beta-diketon class and lactams, more preferably alkyl ketone oximes, phenols, alcohols and pyrazoles, most preferably alkane
Base ketoxime class and pyrazoles.As the object lesson of the unsaturated compound with blocked isocyanate ester group, 2-(O-can be enumerated
[1'-methyl propylene amino] carboxyamino) ethyl propylene acid esters, 2-(O-[1'-methyl propylene amino] carboxyamino) second
Methyl acrylate, 2-[(3,5-dimethyl pyrazole oxazolyl) carbonylamino] ethyl propylene acid esters, 2-[(3,5-dimethyl pyrazole
Base) carbonylamino] ethylmethyl acrylate, 2-[(phthalimide) carbonylamino] ethyl propylene acid esters, 2-be [(adjacent
Phthalimide) carbonylamino] ethylmethyl acrylate, 2-[(butanimide) carbonylamino] ethyl propylene acid esters,
(methyl) acrylic acid 2-isocyanide of the NCO blocks such as 2-[(butanimide) carbonylamino] ethylmethyl acrylate
Base ethyl ester, 2-(O-[1'-methyl propylene amino] carboxyamino) 3-isopropenyl-α, alpha-alpha-dimethyl benzyl ester, 2-(O-[1'-first
Base propylidene amino] carboxyamino) 4-isopropenyl-bis (alpha, alpha-dimethylbenzyl) ester, 2-[(3,5-dimethyl pyrazole oxazolyl) carbonyl ammonia
Base] 3-isopropenyl-bis (alpha, alpha-dimethylbenzyl) ester, 2-[(3,5-dimethyl pyrazole oxazolyl) carbonylamino] 4-isopropenyl-α, α-two
Isopropenyl-bis (alpha, alpha-dimethylbenzyl) the based isocyanate of the isocyano group ester group blocks such as methyl benzyl ester.They can be used alone, also
Can be applied in combination with two or more.It addition, among them, from the point of view of copolymerizable, (the first of preferred isocyanate block
Base) acrylic acid 2-isocyano group ethyl ester.
In copolymer [A], preferably comprise 10mol%～70mol% has blocked isocyanate ester group from (a2)
The repetitive of unsaturated compound, more preferably contains 20mol%～60mol%.If there is blocked isocyanate from (a2)
The repetitive of the unsaturated compound of ester group is less than 10mol%, then thermostability, chemical resistance and electrical property may reduce,
On the other hand, if more than 70mol%, then alkali solubility may become not enough.
Copolymer [A] both can be only to be had blocked isocyanate ester group by (a1) (methyl) crylic acid hydroxylphenyl ester and (a2)
The copolymer that formed of unsaturated compound, it is also possible to be that to be had block by (a1) (methyl) crylic acid hydroxylphenyl ester and (a2) different
The copolymerization that the unsaturated compound copolymerization of cyanic acid ester group obtains and contains other ethylenically unsaturated compounds as copolymer composition
Thing.As other unsaturated compounds, such as acrylic acid, methacrylic acid .beta.-methylacrylic acid, maleic acid, fumaric acid, lemon can be enumerated
Health acid, mesaconic acid, itaconic acid, maleic anhydride, fumaric acid anhydride, citraconic anhydride, mesaconic acid acid anhydride, itaconic anhydride, vinyl benzoate,
Between (methyl) acrylic acid neighbour's carboxyl phenyl ester, (methyl) acrylic acid, carboxyl phenyl ester, (methyl) acrylic acid are to carboxyl phenyl ester, adjacent carboxylic benzene
Base (methyl) acrylamide, a carboxy phenyl (methyl) acrylamide, to carboxy phenyl (methyl) acrylamide, mono succinate [2-(first
Base) acrylyl oxy-ethyl] ester, phthalic acid list [2-(methyl) acryloyl-oxyethyl] ester, ω-carboxy-polycaprolactone list
(methyl) acrylate, 5-carboxyl dicyclo [2.2.1] hept-2-ene", 5,6-dicarboxyl dicyclo [2.2.1] hept-2-ene", 5-carboxyl-
5-methyl bicycle [2.2.1] hept-2-ene", 5-carboxyl-5-ethyl dicyclo [2.2.1] hept-2-ene", 5-carboxyl-6-methyl bicycle
[2.2.1] hept-2-ene", 5-carboxyl-6-ethyl dicyclo [2.2.1] hept-2-ene", 5,6-dicarboxyl dicyclo [2.2.1] hept-2-ene"
Acid anhydride, three ring [5.2.1.02,6] decane-8-base (methyl) acrylate, three ring [5.2.1.02,6] decane-8-base epoxide ethyl (first
Base) acrylate, (methyl) acrylic acid methyl ester., (methyl) ethyl acrylate, (methyl) n-butyl acrylate, (methyl) acrylic acid
Secondary butyl ester, (methyl) tert-butyl acrylate, (methyl) 2-EHA, (methyl) isodecyl acrylate, (methyl) third
The positive lauryl of olefin(e) acid, (methyl) tridecyl acrylate, (methyl) acrylic acid n-octadecane base ester, (methyl) acrylate
Ester, (methyl) acrylic acid 2-methyl cyclohexyl, (methyl) isobornyl acrylate, (methyl) acrylate, (methyl) third
Olefin(e) acid 2-hydroxyl ethyl ester, (methyl) acrylic acid 3-hydroxypropyl acrylate, (methyl) acrylic acid 4-hydroxy butyl ester, diethylene glycol list (methyl) acrylic acid
Ester, (methyl) acrylic acid 2,3-bis-hydroxypropyl acrylate, 2-(methyl) acrylyl oxy-ethyl glucosides, (methyl) phenyl acrylate, (methyl)
Benzyl acrylate, (methyl) acrylic acid O-methoxy phenyl ester, (methyl) acrylic acid meta-methoxy phenyl ester, (methyl) acrylic acid are to first
Epoxide phenyl ester, (methyl) acrylic acid 3-methyl-4-hydroxylphenyl ester, (methyl) acrylic acid 2-methyl-4-hydroxylphenyl ester, (methyl) third
Olefin(e) acid dimethyl oxybenzene ester, ethyl maleate., DEF, diethyl itaconate, dicyclo [2.2.1] hept-2-ene", 5-
Methyl bicycle [2.2.1] hept-2-ene", 5-ethyl dicyclo [2.2.1] hept-2-ene", 5-methoxyl group dicyclo [2.2.1] hept-2-ene", 5-
Ethyoxyl dicyclo [2.2.1] hept-2-ene", 5,6-dimethoxy dicyclo [2.2.1] hept-2-ene", 5,6-diethoxy dicyclo
[2.2.1] hept-2-ene", 5-tert-butoxycarbonyl dicyclo [2.2.1] hept-2-ene", 5-cyclohexyloxy carbonyl dicyclo [2.2.1] hept-
2-alkene, 5-phenyloxycarbonyl dicyclo [2.2.1] hept-2-ene", 5,6-bis-(tert-butoxycarbonyl) dicyclo [2.2.1] hept-2-ene", 5,
6-bis-(cyclohexyloxy carbonyl) dicyclo [2.2.1] hept-2-ene", 5-(2'-ethoxy) dicyclo [2.2.1] hept-2-ene", 5,6-dihydroxy
Base dicyclo [2.2.1] hept-2-ene", 5,6-bis-(methylol) dicyclo [2.2.1] hept-2-ene", 5,6-bis-(2'-ethoxy) dicyclo
[2.2.1] hept-2-ene", 5-hydroxy-5-methyl base dicyclo [2.2.1] hept-2-ene", 5-hydroxyl-5-ethyl dicyclo [2.2.1] hept-2-
Alkene, 5-methylol-5-methyl bicycle [2.2.1] hept-2-ene", styrene, α-methyl styrene, o-methyl styrene, a methyl
Styrene, p-methylstyrene, o-methoxystyrene, meta-methoxy styrene, to methoxy styrene, 1,3-butadiene,
Isoprene, 2,3-dimethyl-1,3-butadiene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide,
Methacrylamide, vinyl acetate, salicyl (methyl) acrylamide, resorcyl (methyl) acrylamide, to oxybenzene
Base (methyl) acrylamide, 3,5-dimethyl-4-hydroxybenzyl (methyl) acrylamide, phenyl maleimide, hydroxy phenyl
Maleimide, N-cyclohexylmaleimide, benzyl maleimide, trifluoromethyl (methyl) acrylate etc..They are permissible
It is used alone, it is also possible to two or more is applied in combination.In order to regulate the transparency, thermostability, attaching, reagent resistance, electrical property,
Refractive index, coating, developability, storage stability, mechanical strength etc., can be in the scope not having undesirable effect each characteristic
In, use these unsaturated compounds with arbitrary proportion.
The weight average molecular weight (Mw) of the copolymer of the present invention is preferably 1500～50000 with polystyrene conversion, more excellent
Elect 2000～20000 as.If weight average molecular weight is less than 1500, then may obtain smooth resin molding, residual after development
Film rate may decline, it is also possible to the pattern form of obtained resin molding and thermostability can be caused to deteriorate, on the other hand, if weight
Average molecular weight is more than 50000, then sensitivity may decline, and pattern form may deteriorate.
Additionally, the value of the molecular weight of the copolymer of the present invention is calculated by following manner: use gel permeation chromatography (GPC)
It is measured with following condition, is calculated by polystyrene conversion.To start the time started from GPC to 21 minutes as calculating
Scope, calculates weight average molecular weight and molecular weight distribution.
Post: Showa electrician (Shodex, registered trade mark) KF-801+KF-802+KF-802+KF-803
Column temperature: 40 DEG C
Leacheate: oxolane
Detector: differential refractometer (Showa electrician (registered trade mark) RI-101)
Flow velocity: 1mL/ minute
Have no particular limits for obtaining the copolyreaction of the copolymer of the present invention, radical polymerization, sun can be enumerated
Ionic polymerization, anionic polymerisation, coordinated anionic polymerization etc..Specifically, with (a1) (methyl) crylic acid hydroxylphenyl ester and
(a2) have the unsaturated compound of blocked isocyanate ester group be neccessary composition and the most preferably amount to 10 mass %～
The scope of 60 mass % contains in the reaction dissolvent of other unsaturated compounds, it is possible to use polymerization initiator is polymerized.Point
The adjustment of son amount can realize by adjusting the usage amount of reaction dissolvent, the usage amount of initiator and polymerization temperature.It addition, point
The adjustment of son amount can also realize by using the chain-transferring agent with thio-alcohol as representative.
As the object lesson of reaction dissolvent, can enumerate methanol, ethanol, 1-propanol, isopropanol, butanol, ethylene glycol, third
Ketone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), oxolane, dioxane, toluene, dimethylbenzene, ethyl acetate, isopropyl acetate, second
Acid n-propyl, butyl acetate, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, ethylene glycol monoethylether acetate, second
Methoxy butyl acetate, ethylene glycol monobutyl ether acetas, diethylene glycol monoethyl ether acetas, the diethyls such as acid 3-methoxybutyl
Glycol monobutyl ether acetas, propylene glycol monomethyl ether, ethylene glycol mono-ether, 3-methoxybutanol, diethylene glycol monoethyl ether, diethylene glycol
Monobutyl ether, dimethyl sulfoxide, dimethylformamide, dimethyl acetylamide, ethyl lactate, diethylene glycol ethyl methyl ether, diethyl
Glycol dimethyl ether, methoxy methyl propionate, ethoxyl ethyl propionate etc..
As polymerization initiator, can enumerate such as: 2,2'-azos two (2,4-methyl pentane nitrile), 2,2'-azo two
(2-butyronitrile), 2,2'-azodiisobutyronitrile, dimethyl-2,2'-azo-bis-iso-butyl, 1,1'-azo two (hexamethylene-1-nitrile)
Deng azo initiator, or benzoyl peroxide, lauryl peroxide, caprylyl peroxide, acetyl peroxide, di-t-butyl mistake
Oxide, tert-butyl cumyl peroxide, dicumyl peroxide, tert-butyl peroxy acetate, t-butyl peroxybenzoate
Deng organic peroxide.
In the photosensitive polymer combination of the present invention, the compound with quinone diazido contained as neccessary composition
[B] is photosensitizer, as long as have the compound of quinone diazido, then there is no particular limitation.Preferably can enumerate such as: energy
Enough esters being condensed with 1,2-naphthoquinone two nitrine sulfamic acid halide by phenolic compound or alcohol compound and obtaining.Wherein, from
From the point of view of the transparency of photonasty and resin molding, relative to the hydroxyl in phenolic compound or alcohol compound, more excellent
Choosing makes to be equivalent to the 1 of 30～85mol%, the ester that 2-naphthoquinone two nitrine sulfamic acid halide is condensed, and most preferably makes to be equivalent to 50
～the ester of the 1,2-naphthoquinone two nitrine sulfamic acid halide condensation of 70mol%.As this phenolic compound or alcohol compound
Object lesson, 2,3,4-trihydroxybenzophenones, 2,4,6-trihydroxybenzophenones, 2,2', 4,4'-tetrahydroxys can be enumerated
Benzophenone, 2,3,4,3'-tetrahydroxybenzophenone, 2,3,4,4'-tetrahydroxybenzophenone, 2,3,4,2'-tetrahydroxy-4'-
Methyl benzophenone, 2,3,4,4'-tetrahydroxy-3'-methoxy benzophenone, 2,3,4,2', 6'-pentahydroxybenzophenone, 2,
4,6,3', 4', 5'-hexahydroxy benzophenone, 3,4,5,3', 4', 5'-hexahydroxy benzophenone, 2-methyl-2-(2,4-dihydroxy
Base phenyl)-4-(4-hydroxy phenyl)-7-hydroxychroman, 2-[double { (5-isopropyl-4-hydroxy-2-methyl) phenyl } methyl] benzene
Phenol, 1-[1-(3-{1-(4-hydroxy phenyl)-1-Methylethyl }-4,6-dihydroxy phenyl)-1-Methylethyl]-3-(1-(3-
{ 1-(4-hydroxy phenyl)-1-Methylethyl }-4,6-dihydroxy phenyl)-1-Methylethyl) benzene, double { 1-(the 4-hydroxy benzenes of 4,6-
Base)-1-Methylethyl double (2,4-dihydroxy phenyl) methane of-1,3-Benzodiazepines, double (p-hydroxybenzene) methane, three (to hydroxyl
Phenyl) methane, 1,1,1-tri-(p-hydroxybenzene) ethane, double (2,3,4-hydroxy phenyl) methane, double (the 2,3,4-trihydroxy of 2,2-
Phenyl) propane, 1,1,3-tri-(2,5-dimethyl-4-hydroxy phenyl)-3-phenyl-propane, 1-[1-(4-hydroxy phenyl) isopropyl
Base]-4-[1,1-double (4-hydroxy phenyl) ethyl] benzene, double (2,5-dimethyl-4-hydroxy phenyl)-2-hydroxy phenyl methane, 3,
3,3', 3'-tetramethyl-1,1'-spirobindene-5,6,7,5', 6', 7'-hexanol, 2,2,4-trimethyl-7,2', 4'-trihydroxy is yellow
Alkane etc..They may be used alone, two or more kinds can also be used in combination.As having the compound [B] of quinone diazido, excellent
Select the 1,2-naphthoquinone two nitrine sulfonic acid of 1-[1-(4-hydroxy phenyl) isopropyl]-4-[double (4-hydroxy phenyl) ethyl of 1,1-] benzene
Ester.
In the photosensitive polymer combination of the present invention, relative to 100 mass parts copolymers [A] (solid phase components), have
The addition of the compound [B] of quinone diazido is preferably 5 mass parts～60 mass parts, more preferably 10 mass parts～50 matter
Amount part.If there is the addition of compound [B] of quinone diazido less than 5 mass parts, then may result in development the best, another
Aspect, if more than 60 mass parts, then may result in development the best, also can make the transparency of resin molding, insulating properties and flatness
It is deteriorated.
Although the photosensitive polymer combination of the present invention contains copolymer [A] and has the compound [B] of quinone diazido
As neccessary composition, but in the range of the effect not damaging the present invention, as required, UV absorbent, increasing can be contained
Sense agent, sensitizing auxiliary agent, plasticizer, thickening agent, organic solvent, dispersant, defoamer, surfactant, attaching auxiliary agent, temperature-sensitive
Property acid-producing cpd and copolymer [A] and there is the compound that compound [B] cross-linking reaction of quinone diazido obtains.
It addition, the photosensitive polymer combination of the present invention is by by copolymer [A] and the chemical combination with quinone diazido
Thing [B] and other compositions that can arbitrarily add as above uniformly mix and prepare, it is possible to suitable molten to be dissolved in
Agent uses with solution state.
As solvent, it is possible to use make copolymer [A] and there is the compound [B] of quinone diazido and can arbitrarily add
Other composition uniform dissolution added and the solvent not reacted with each composition, can enumerate and can be used in preparation altogether with above-mentioned conduct
Identical solvent illustrated in the solvent of polymers [A].Wherein, it is contemplated that the dissolubility of each composition and the reactivity of each composition, painting
The aspects such as the easy degree that film is formed, it may be preferred to use diethylene glycol ethyl methyl ether, diethylene glycol dimethyl ether, propylene glycol list
Methyl ether, propylene glycol methyl ether acetate, methoxybutyl acetas, methoxy methyl propionate and ethoxyl ethyl propionate.It addition,
In order to improve thickness uniformity in face, can N-Methyl pyrrolidone used along with these solvents, gamma-butyrolacton, N,
The high boiling solvents such as N-dimethyl acetylamide.
During with the photosensitive polymer combination of the solution state preparation present invention, relative to copolymer [A] (solid phase components) and
The compound [B] with quinone diazido and total amount 100 mass parts of other compositions that can arbitrarily add, it is possible to 30 matter
Amount part～4000 mass parts, preferably 50 mass parts～3000 mass parts are added above-mentioned solvent and (be can be used alone, it is also possible to 2
Plant combination of the above to use).
Owing to the coating of photosensitive polymer combination, developability, curable and the storage stability of the present invention are good, logical
Cross and use this photosensitive polymer combination, it is possible to form thermochromism transparent, resistance to and the resin molding of excellent electrical property.This resin
Film can be applicable to be formed the protecting film of electronic unit, planarization film or interlayer dielectric, and forms lenticule or micro-
Lens array, forms light scattered reflection film, tropism control projection or the interval of liquid crystal display cells, forms color filter or light wave
Guide passage.
Below the forming method of the resin molding of the photosensitive polymer combination employing the present invention is illustrated.First,
At glass substrate, silicon chip and be formed over their surface on the substrate of various metal, the photonasty tree of the coating present invention
Oil/fat composition so that it is be dried, forms radiosensitivity resin molding.As the coating process of photosensitive polymer combination, there is no spy
Other restriction, can enumerate the suitable methods such as spraying process, rolling method, spin-coating method, stick coating method, slot coated method.Drying condition
Kind according to each composition, use ratio etc. and different, but can be set to carry out 30 seconds～30 at 60 DEG C～110 DEG C
About minute.
Then, on the resin molding formed, across having the mask of specific pattern, after irradiating with lonizing radiation, by making
Carry out development treatment with developer solution, the formation of pattern can be carried out.As the lonizing radiation now used, such as g line can be enumerated
(wavelength is 436nm), i line (wavelength is 365nm), KrF excimer laser, ArF excimer laser, X-ray, electron beam etc., make
For its light source, low pressure mercury lamp, high voltage mercury lamp, ultrahigh pressure mercury lamp, chemical lamp, excimer laser generating means etc. can be enumerated.Make
For the developer solution for development treatment, it is possible to use such as sodium hydroxide, potassium hydroxide, sodium silicate, sodium metasilicate, ammonia, ethamine,
N-propylamine, diethylamine, diethylaminoethanol, di-n-propylamine, triethylamine, methyl-diethyl-amine, dimethylethanolamine, triethanolamine,
Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide, pyrroles, piperidines, 1,8-diazabicyclo [5,4,0]-ten one carbon-7-alkene, 1,
The aqueous solution of the alkali (alkali compounds) such as 5-diazabicyclo [4,3,0]-nonyl-5-alkene.Furthermore, it is possible to water-soluble by described alkali
Liquid is added with the water-miscible organic solvent such as methanol, ethanol or the aqueous solution of surfactant in right amount or is dissolved with sense of the present invention
The various organic solvents of photosensitive resin composition use as developer solution.It addition, as developing method, it is possible to use full liquid method
(liquid is containedMethod), infusion process, shake infusion process, the suitable method such as spray process.Developing time now is according to photoresist
The composition of compositions and different, but such as 30 seconds～120 seconds can be set to.
It follows that for the resin molding forming pattern, it is preferred that such as utilize circulating water to clean and be rinsed processing,
It is more preferable that by irradiating with lonizing radiation comprehensively, carry out in this resin molding residual has quinone diazido
The resolution process of compound [B].Constitute the reason of extinction owing to having the compound [B] of quinone diazido, therefore pass through afterwards
The transparency of exposure resin molding is improved.
It follows that be by utilizing hot plate (hot plate), baking oven etc. to carry out heat treated (rear baking process), thus can
To carry out cured.The sintering temperature of this cured is such as 120 DEG C～250 DEG C.Heat time heating time is according to heating machine
Kind and different, but, such as when carrying out heat treated on hot plate, can be set to 5 minutes～30 minutes, in an oven
When carrying out heat treated, 30 minutes～90 minutes can be set to.Particularly when forming lenticule and tropism control projection, also
The substep baking process (step baking method) carrying out more than twice heating process can be used, specifically, at pattern
Carry out initial stage heating at a temperature of more than the glass transition temperature of the resin molding changed and make pattern flow, because surface tension becomes
Hemispherical, then, heating cross-links at higher temperatures, thus forms specific shape.
It is possible to be formed on a surface of a substrate with as the protecting film of target, planarization film, interlayer dielectric, micro-
The various uses such as mirror or microlens array, light scattered reflection film, tropism control projection, interval, color filter, optical waveguide are relative
Pattern-like thin film.The resin molding being thusly-formed, its thermochromism transparent, resistance to and electrical characteristics are excellent.
[embodiment]
Embodiment is illustrated below and the present invention is specifically explained by comparative example, but the invention is not limited in following reality
Execute example.
<synthesis of copolymer>
[embodiment 1]
In the flask equipped with reflux condenser and agitator, add 42 mass parts methacrylic acid para hydroxybenzene esters, 58
Mass parts 2-(O-[1'-methyl propylene amino] carboxyamino) ethylmethyl acrylate, 400 mass parts propylene glycol monomethyl ethers
Acetas and 6 mass parts 2,2'-azodiisobutyronitrile, after replacing with nitrogen, make liquid temperature rise to 80 DEG C while stirring, at 80 DEG C
Lower reaction 6 hours.Confirmed the disappearance of monomer by gel permeation chromatography, be warming up to 100 DEG C, carry out ageing in 30 minutes.80
DEG C, decompression under conditions of, be removed by distillation propylene glycol methyl ether acetate, solid phase components concentration be adjusted to 30 mass %,
Obtain the resin solution (S-1) containing copolymer [A-1].
The copolymer [A-1] contained in resin solution with the weight average molecular weight (Mw) of polystyrene conversion for 8700, molecule
Amount distribution (Mw/Mn) is 3.5.
[embodiment 2]
In the flask equipped with reflux condenser and agitator, add 41 mass parts methacrylic acid para hydroxybenzene esters, 59
Mass parts 2-[(3,5-dimethyl pyrazole oxazolyl) carbonylamino] ethylmethyl acrylate, 400 mass parts propylene glycol monomethyl ether second
Acid esters and 6 mass parts 2,2'-azodiisobutyronitrile, react in the same manner as example 1, obtain containing copolymer
The resin solution (S-2) of [A-2].
The copolymer [A-2] contained in resin solution with the weight average molecular weight (Mw) of polystyrene conversion for 8800, molecule
Amount distribution (Mw/Mn) is 3.5.
[embodiment 3]
In the flask equipped with reflux condenser and agitator, add 36 mass parts methacrylic acid para hydroxybenzene esters, 51
Mass parts 2-(O-[1'-methyl propylene amino] carboxyamino) ethylmethyl acrylate, 13 mass parts methacrylic acids are just
Butyl ester, 400 mass parts propylene glycol methyl ether acetates and 6 mass parts 2,2'-azodiisobutyronitrile, with same as in Example 1
Mode is reacted, and obtains the resin solution (S-3) containing copolymer [A-3].
The copolymer [A-3] contained in resin solution with the weight average molecular weight (Mw) of polystyrene conversion for 8300, molecule
Amount distribution (Mw/Mn) is 3.3.
[comparative example 1]
In the flask equipped with reflux condenser and agitator, add 56 mass parts methacrylic acid para hydroxybenzene esters, 44
Mass parts glycidyl methacrylate, 600 mass parts propylene glycol methyl ether acetates and 6 mass parts 2,2'-azos two are different
Butyronitrile, after replacing with nitrogen, makes liquid temperature rise to 80 DEG C while stirring, reacts 6 hours at 80 DEG C.Pass through gel permeation chromatography
Method confirms the disappearance of monomer, is warming up to 100 DEG C, carries out ageing in 30 minutes.100 DEG C, decompression under conditions of, be removed by distillation
Propylene glycol methyl ether acetate, is adjusted to 30 mass % by solid phase components concentration, obtains the resin containing copolymer [A'-4] molten
Liquid (S-4).
The copolymer [A'-4] contained in resin solution with the weight average molecular weight (Mw) of polystyrene conversion for 8400, molecule
Amount distribution (Mw/Mn) is 3.1.
<evaluation>
(1) transparency
On the glass substrate, coating resin solution (S-1)～(S-4) make thickness be 3 μm, are dried 30 with 80 DEG C in an oven
Minute.For the obtained glass substrate with resin molding, use spectrophotometer, with glass substrate as blank, survey
Minimum transmitance under standing wave a length of 400～800nm.Transmitance is the biggest, and the transparency is the highest.Result is shown in Table 1.
(2) curable
On the hot plate of 150 DEG C, coating resin solution (S-1)～(S-4) make thickness be about 0.5mm, measure to gelation
The required time.Time is the shortest, and curable is the best.Result is shown in Table 1.
(3) electrical property
On metallic substrates, coating resin solution (S-1)～(S-4) make thickness be 3 μm, are dried 30 with 80 DEG C in an oven
Minute.In the baking oven of 200 DEG C, carry out dry film 30 minutes being heating and curing.Solidification obtained by measuring under 1MHz
The dielectric constant of film.Dielectric constant is the least, and electrical property is the best.Result is shown in Table 1.
[table 1]
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Comparative example 1 | |
| The transparency | 99% | 99% | 99% | 99% |
| Gelation time | 85 seconds | 108 seconds | 93 seconds | 163 seconds |
| Dielectric constant | 3.6 | 3.3 | 3.5 | 4.5 |
<preparation of photosensitive polymer combination>
[embodiment 4]
Resin solution (S-1) that 100 mass parts are obtained in embodiment 1,6.25 mass parts 1-[1-(4-hydroxy phenyl)
Isopropyl]-4-[1,1-double (4-hydroxy phenyl) ethyl] benzene-1,2-naphthoquinone two nitrine-5-sulphonic acid ester and 75 mass parts propylene glycol
Methyl ether acetate mixed dissolution, filters with the membrane filter of 0.2 μm, prepares the photosensitive polymer combination of solution state
(S-5)。
[embodiment 5]
Use the resin solution (S-2) obtained in example 2, in the way of the same as in Example 4, prepare solution state
Photosensitive polymer combination (S-6).
[embodiment 6]
Use the resin solution (S-3) obtained in embodiment 3, in the way of the same as in Example 4, prepare solution state
Photosensitive polymer combination (S-7).
[comparative example 2]
Use the resin solution (S-4) obtained in comparative example 1, in the way of the same as in Example 4, prepare solution state
Photosensitive polymer combination (S-8).
<evaluation>
(1) storage stability
After photosensitive polymer combination (S-5)～(S-8) at room temperature being preserved 1 month, measure its viscosity.Additionally, it is viscous
Degree uses E type viscometer to be measured at 25 DEG C.Relative to viscosity when just preparing, after at room temperature preserving 1 month
The climbing of viscosity be designated as zero in the situation less than 10%, the situation more than 10% is designated as ×.Result is shown in Table 2.
(2) coating
On the glass substrate, photosensitive resin coating compositions (S-5)～(S-8) make thickness be 3 μm, in an oven with 80
DEG C be dried 30 minutes.All photosensitive polymer combination all obtains transparent resin film in uniform thickness, and coating is good (zero).
(3) developability
The resin molding being dried is exposed with ultrahigh pressure mercury lamp across erect image mask (Positive pattern mask),
Within in the aqueous solution of the Tetramethylammonium hydroxide that impregnated in 2.38 weight % 1 minute, develop, be rinsed by purified water.All
Photosensitive polymer combination has all transferred erect image, and developability is good (zero).
(4) transparency
The resin molding being dried does not carries out blanket exposure across erect image mask, carries out heating in 30 minutes with 200 DEG C in an oven
Solidification.For the obtained glass substrate with cured resin film, use spectrophotometer, right with glass substrate for blank
According to, measuring wavelength is the minimum transmitance under 400～800nm.Transmitance is the biggest, and the transparency is the highest.Result is shown in Table 2.
(5) resistance to thermochromism
After carrying out 30 minutes being heating and curing at 200 DEG C, then at 230 DEG C, carry out 10 minutes heat treated, with glass base
Plate is blank, and measuring wavelength is transmitance during 400nm.Transmitance is the biggest, and resistance to thermochromism is the highest.Result is shown in table 2
In.
Table 2
| Embodiment 4 | Embodiment 5 | Embodiment 6 | Comparative example 2 | |
| Storage stability | ○ | ○ | ○ | ○ |
| Coating | ○ | ○ | ○ | ○ |
| Developability | ○ | ○ | ○ | ○ |
| The transparency | 99% | 99% | 99% | 99% |
| Heat-resisting amyloidogenic | 84% | 88% | 85% | 70% |
Claims (8)
1. a photosensitive polymer combination, it is characterised in that containing copolymer and the compound with quinone diazido, described
Copolymer comprises from the repetitive of (methyl) crylic acid hydroxylphenyl ester with from the unsaturation with blocked isocyanate ester group
The repetitive of compound.
2. photosensitive polymer combination as claimed in claim 1, it is characterised in that containing described in 30mol%～90mol%
Described from having blocked isocyanate from the repetitive of (methyl) crylic acid hydroxylphenyl ester and 10mol%～70mol%
The repetitive of the unsaturated compound of ester group.
3. photosensitive polymer combination as claimed in claim 1 or 2, it is characterised in that described in there is blocked isocyanate ester group
Unsaturated compound be block (methyl) acrylic acid 2-isocyano group ethyl ester.
4. photosensitive polymer combination as claimed in claim 1 or 2, it is characterised in that described block is by methyl ethyl ketone
The block that oxime causes.
5. photosensitive polymer combination as claimed in claim 1 or 2, it is characterised in that described in there is blocked isocyanate ester group
Unsaturated compound be 2-(O-[1'-methyl propylene amino] carboxyamino) ethyl (methyl) acrylate.
6. photosensitive polymer combination as claimed in claim 1 or 2, it is characterised in that described common relative to 100 mass parts
Polymers, it contains the compound described in 5～60 mass parts with quinone diazido.
7. photosensitive polymer combination as claimed in claim 1 or 2, it is characterised in that relative to the composition beyond solvent
Total amount 100 mass parts, it contains the solvent of 30～4000 mass parts.
8. a resin molding, it is characterised in that it is for being applied to base by the photosensitive polymer combination described in claim 1 or 2
On plate, it is dried and obtains.
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| JP2012-273067 | 2012-12-14 | ||
| PCT/JP2013/077643 WO2014091818A1 (en) | 2012-12-14 | 2013-10-10 | Copolymer and photosensitive resin composition and resin film containing said copolymer |
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| JP2006307129A (en) * | 2005-03-30 | 2006-11-09 | Asahi Glass Co Ltd | Oil-repellent composition and oil-repellent film |
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